


Chance Meetings

by AmeliaSPN1973



Category: Supernatural
Genre: Dinner, F/M, Not Beta Read, Romance, Smut, date, plus size reader
Language: English
Status: Completed
Published: 2019-02-05
Updated: 2019-02-05
Packaged: 2019-10-22 15:17:12
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 11,280
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17664998
Author URL: https://archiveofourown.org/users/AmeliaSPN1973/pseuds/AmeliaSPN1973
Summary: Your friend convinces you to get out of the house and go to a bar where you come across Dean and Sam Winchester.





	1. Chapter 1

It was Friday night around eight pm. You had just showered and were now all curled up on your couch in your favorite pair of jammies and socks, turning on the TV and looking at the what’s on. After realizing there wasn’t much on live TV worth watching, you went to the DVR menu and decided it was time to binge watch that show your friend was telling you about, but never had the chance to watch, the nineteenth century woman that goes through time traveling stones into eighteenth century Scotland where she hooks up with a handsome ginger.

You were on the wedding episode when there was loud knocking at your door. You pause the show right at the beginning of the wedding night sex scene and get up slowly and went to the door.

Your best friend Angelica barges in as you answer the door. “Come On Y/N. We’re going out.”

“I’m not really in the mood to head out tonight Angelica.”

She looks over at the TV and laughs. “Girl, why watch porn when you can have it?”

“First, Outlander is not porn. Secondly, I’m not really in the mood for either, but trying to catch up on my show.”

“Too bad. So sad. Go get dressed.” There is no winning an argument with Angelica when she has her mind determined on something. “Put on that black cocktail dress you love so much. It looks so great on you.”

You smile. She means well. You head back to your room and begin looking in your closet. You find your dress in the back corner and get it out. You hadn’t worn it in awhile and wonder if it will fit. You’ve gained a few pounds (by few you mean about ten) since the last time you wore it. Thank goodness it is stretchy, goes on not too tight and only clingy where it needs to be. You brush your teeth, brush your hair, and apply minimal makeup: a tinted lotion, setting powder, mascara, blush and lip gloss sets your face. You grab your purse and head back into the living room where Angelica waits.

“You look great Y/N. Maybe you’ll finally get laid. It’s been long enough. You ready?” She laughs as she says it. She knows you haven't been yourself lately. Depression and anxiety seem to rear their ugly heads a lot, but you keep moving forward.

After arguing who drives, you decide to go together in your Malibu so you can drive home when Angelica gets lucky.

You get to the Wayward Pub and park your car. You notice a sleek 1967 black Chevy Impala in the parking lot next to you and you’re impressed. _Whoever owns this car really takes care of it._

You go in and try to sit in a back corner booth but Angelica won’t have it. “Let’s sit at a table in the middle. You won’t get noticed sitting in the corner.”

“That’s what I was hoping for.”

“Y/N. You’re never gonna get laid again if you don’t try.” She gets up. “I’m gonna get us drinks. You want your usual? Margarita?”

“Yeah. Thanks.”

You look around and see a gorgeous guy walking up to the bar at the same time as Angelica. He’s rugged yet devastatingly handsome in a nice three piece black suit; about six feet tall; short brown hair with flecks of dirty blonde; perfectly symmetrical face, five o’clock shadow, and pouty kissable lips. He looked like he walked right out of a GQ magazine.

He looks over and your eyes lock a moment. He winks, and you smile shyly, immediately looking down; you’re turned on immediately.  You watch him go up to the bar and begin ordering drinks. The bartender hands him 2. You then see Angelica saddling up beside him and begins talking. _Damn! I should have said something first,_ but you didn’t.

He wouldn’t be into you anyway. Angelica is probably more his type. She’s brunette, tan, with a slimmer figure and bigger breasts than you. She’s gorgeous and you are more a Duff.

You look back down, staring at the table top, as you think of ways you can sneak out of the bar before they come back, but before you know it, Angelica was right back at the table with the handsome man in tow.  She sets down your margarita and her vodka tonic.

“Y/N, this is Dean. He’s buying us our drinks tonight.”

“Hey.” He smiles and his smile is perfect too with perfect teeth. He takes your hand and you look up and smile shyly again, pink creeping into your cheeks. “Hi, and Thanks.”

“You’re welcome.” He continues smiling at you with your hand in his for a little too long and you can just feel the heat rising in your body. He then looks over towards the other side of the room. “Just a given me a moment sweethearts,” he says to Angelica, letting go of your hand and steps away a few minutes.

When Dean returns, he has an even taller friend with him with long flowing hair, like something out of a Harlequin Romance novel cover. He’s wearing a suit and you can tell he is younger. You immediately feel like the old maid at this table. Dean introduces him. “This is my partner and  brother, Sam.”

“Hi.” You smile and he smiles back shyly as well.

Angelica smiles, but you can see that her focus has now shifted from the devastatingly handsome Dean to Sam.

“Hi Sam,” Angelica says as she puts her hand in his. “Come sit down with us,” she says.

She sits across from you and Sam sits across from Dean next to her while Dean slides in next to you.

Your heart begins beating faster and irregularly as your body heat continues to rise.

Angelica starts the conversation. “So, what are two handsome devils like you doing in our little ol’ town.”

“Working a case,” Dean says pulling out his badge, showing you as you turn your head towards him. It says FBI and Homeland Security on it. Government men. Your breath hitches because your so close to his beautiful face and those kissable lips. He smiles and you swallow hard.

“Glad to know get to have some time off for the evening.” You take a drink of your margarita.

“So, what do you two do?” Dean asks you and Angelica but he focuses his eyes on you; his piercing green eyes look deep into yours and you almost forget to speak.

“Customer service. Phone Agent,” you say. “Pays the bills. I went to law school, but didn’t become a lawyer.”

Sam smiles. “I almost went to law school, but decided to go into the family business with my brother here instead.”

“You didn’t miss much.” You realized after attending law school, you were not the lawyer type.

Angelica smiles. “Phone sex operators.” She then busts out laughing.

You kick her shin under the table. “We are not phone sex operators.”

Dean smiles. “Well, you have a nice voice Y/N. I’d find it deeply distracting to try to get any business done if I had to talk to you on the phone. You may as well be.”

“Thanks.” Your cheeks get redder and your mouth gets super dry at his compliment. You suck a large amount of your drink and now you’re envisioning your mouth on him, so you shift in your seat from the arousal. You then take another big swig and you’ve already downed your first margarita.

“I’ll get you another,” Dean says.

“No thanks,” you smile. “I’ll just get a water please.”

“OK. Anyone else?” Dean got up.

Everyone else said no, so he walked up to the bar and brought you back a water, another beer for himself, and also some menus. “Anybody hungry?”

“Starved,” you say. “They have great burgers here.”

“They do?” Dean smiles and nods to Sam. “I do love a good burger.”

Sam smiles. “That he does.”

A few minutes later a waitress came over. “What can I get you all?”

She looks at you first. “I’ll have the bacon pepperjack chipotle burger with onion rings and the chipotle ranch dressing please.”

Dean looks at you and smiles. “Nice choice.”

The waitress looks at Angelica. “I’ll have the chicken Caesar salad.” She’s the typical date type, eating salad. You’ve seen her slam a triple pepperjack chipotle burger when she’s not on the prowl for a man or a shag, but not in front of good looking men. You weren’t meant to be bothered. If he doesn’t like you or what you eat, it’s his problem, not yours.

Sam was next. “I’ll have the same thing as she.” He looks over at Angelica.

Dean groans. “Salad. Really Sammy?”

“I like to be healthy,” Sam says.

You laugh at Dean calling his brother by Sammy. They are definitely brothers.

When the waitress gets to Dean he looks at you and smiles. “You know I’ll have the same thing as she is having, only make mine a double burger instead, please.”

Sam and Angelica begin talking quietly to each other, while waiting for your food, as you look down at your empty water glass.

Dean looks over at you. “So, I have to say you look really good in that dress.”

“Thanks.” Your temperature is borderline feverish.

“You are really quite beautiful.” You turn and he’s staring deep in your eyes.

“And Wow, you are just…” You swallow hard. You’re stuttering and rambling. “You have amazing green eyes.”

“Thanks.” He smirks and you shift in your seat as you feel your arousal soaking your panties.

_Damn! He’s so gorgeous._

“So, how old are you Dean?”

Dean looks at you honestly. “Just turning 40 this year.”

“Well, welcome to Club 40s.” You smile.

“Really. You don’t look it.”

“I’m actually going on 46 in two months.”

“Wow! You don’t look a day over 30.”

“Well Thanks.”

“Y/N has a baby face. I’m always being told I’m the older friend,” Angelica says. “She got good genes.”

“Thanks.” Thank goodness you did not use too much blush, because you are sure your face is beet red.

Finally, the food arrives and you are glad for the reprieve from having to look into those sexy eyes and face. You know that if he wanted to, he could have you on the table, pounding into you while everyone watched and you would not care. You’re usually are not like that. You haven’t been with anyone since you broke up with Joe almost a year ago. He was bad news and it took this entire last year for you to get up the nerve to start going out again, let alone dating and sex.

You take a large bite of your burger and you can thank this time that you can just eat.

Dean takes a large bite and begins talking with his mouth full. “You weren’t kidding. This burger is amazing. Definitely another reason to come back.” He looks at you as he says it.

You nod.

You continue eating, trying to get your body heat down, but the food just makes you feel hotter.

You finish your burger and onion rings and take a drink of your new glass of water.

Dean looks at you and smiles. “Wanna get out of here; go somewhere we can talk?”

You pull away from your water and stare in his eyes. You want him like you haven’t wanted anyone, even Joe. You look at Angelica, who is smiling. Turning back to Dean, “OK. I’ll just run to the ladies room and will be right back.”

Angelica gets up with you and you two walk to the restroom. As soon as you get in and the door shuts you begin to breathe heavily as you stare in the mirror. “I don’t know if I can do this Angelica.”

She grabs you square on your shoulders and stares at you. “You can do it. He’s gorgeous; he’s charming; and he is super into you. Plus, if I didn’t know better, he really wants to fuck you.”

“Really?”

“Oh my God Y/N. He likes you. I mean I wish I was the one he wanted to go home with, but Sam is hot and closer to my age.” You and Angelica were best friends, but you were eight years older.

“Yeah. I thought I’d get saddled with the younger guy and feel like a cougar. I mean Dean’s 40 and I feel like a cougar.”

“Don’t be. He likes you. You are going to have so much fun. I just know it.”

You take deep breaths. It had been so long since you had sex with someone and someone you barely knew. You apply fresh lip gloss and translucent powder.

Angelica stares at you. “You are going to be great. I bet you with someone like him, you won’t have to work too hard. Trust me. Hot guys that go from town to town want to keep those connections for when they come back through. I can tell he is a giver and he’s going to make sure you have fun all night.”

“How do you know?”

“I just feel it Y/N.” She reaches in her purse and hands you 2 condoms.

“I have a few at home already Angelica.”

“Don’t worry. I still have six more. If Sam is anything like Dean, I think I’m gonna need all of these tonight. Now. I need to borrow your car?”

“OK.” You hand Angelica your keys.

“Thanks Y/N.” She smiles big. “Let’s not leave our dates waiting.”

You walk back out and Dean and Sam are still sitting at the table, but when he sees you, he immediately gets up. “I already paid.” There was a tip on the table.

“Thanks.” You smile.

“No problem. Shall we?” He gestures you to walk first and places his hand on your back which makes you shiver.

You get outside and he begins directing you to his car, the 1967 Impala.

“So, you are the owner of this beaut.”

“Yep.” He smiled.

“I looked at it while when we pulled up and headed in.”

Angelica smiles. “Yeah. She has a thing for hot guys driving classic, fast cars.”

“You do?” Dean cocks his eyebrows and smirks.

“I do like a fast car.” Smiling,

He walks over to the passenger door and opens it for you.

“Thanks.” You climb in and see it’s really well maintained.

Angelica yells “Talk to you tomorrow.”

“OK. You too. Night.” You turn back to Dean. “You keep good care of it.”

“I do,” he said as he shuts the door and then walks over getting into the passenger side.


	2. Chapter 2

It was a short drive to your house. You let him pull into your garage because you live near family and you didn’t want them to know you were inviting a strange man back to your home.

You get out walking over to the door leading to your house when he approaches and looks right

at you. “I’ve really wanted to kiss you all night. May I?”

Even in your messed up head, you wanted him too as well. “OK.”

He places his palms against both sides of your face, turns his head as he leans in, pressing his lips to yours. 

His lips were supple and soft. He begins moving his lips slowly against yours as he pulls between your upper and lower lips. You find yourself sucking on his lower lip and you find yourself moaning.

“Wow,” you say as you pull away.

“Yeah,” he said as you caught your breaths and he leaned into you again. 

This time, your kissing becomes needy as your hands run up around his neck and into his hair and his hands run up and down your spine, pressing you closer to him. You can feel his bulge against you and it turns you on. 

“I want you,” he says honestly as he pulls his face away and looks into your eyes. He’s still pressed against you..

You haven’t wanted someone so much in your life as you stare into his green eyes. His lips tell you he’s experienced in what he is doing and you want to feel more. “Yes. Want you too.”

He engulfs your mouth again with his as he reaches down dragging the end of your dress up your thigh until he reaches a buttock and squeezes. 

You moan as he slips his hand inside the back of your panties and continues squeezing a cheek. 

“Yes.” You moan into his mouth. 

He reaches down as his hand moves up your other thigh until both hands are squeezing your buttocks.

He grabs your thighs raising them as you wrap them around his waist and his hands return to holding and squeezing your buttocks hard. “Hold on,” he says as your arms tighten around his neck and he begins carrying you into your house.

He first carries you to the kitchen counter as he presses you against it, taking a breather, and kissing you passionately. You can feel his bulge getting bigger and your mouth’ anticipating being around his cock.

_ Who are you? _ You have never felt this forward before. You never enjoyed blow jobs, but they were an unnecessary evil of foreplay, but Dean makes you want to.

“What are you thinking about?” He looks at you and can see your gears turning. 

_ Should I be honest?  _ “I want you in my mouth.”

“You do?” He smirks and cocks his head. 

“”Yes,” You breathily speak. You swallow the pool of saliva in your mouth and he notices.  _ Boy does he notice.  _ You feel the tent in his jeans get larger. He shoves his tongue in your mouth as they fight for dominance.

He carries you to the living room and he sits down on your couch as you straddle him making out for awhile. When you feel the kiss beginning to end, you slide down his body to your knees. You spread his legs as you move between them. 

You undo his belt; unbutton and unzip his suit pants as you move the hole of his boxer briefs open and let his erection spring free. You gasp at the length and the girth and wonder how you are going to take that when he thrusts into you. 

Leaning in, you lick up the main vein running underneath as you hear his breath hitch. You begin to swirl along the tip with your tongue as you grip around him at the bottom,

squeeze and turn. 

“Yes.” He says with a grunt. 

You continue swirling your tongue around the tip, finally taking him in your mouth inch by inch until he reaches the back of your throat. Relaxing your gag reflex, you press your tongue along him, moving him to the roof of your mouth, and begin to suck. 

“Oh Geez Y/N.” 

Your hand continues turning, giving him the friction he needs, while the other massages his balls.

“I’m gonna cum soon.”  

You feel him pulsing in your mouth. He reaches down holding your head as he thrusts into your mouth. You gasp a deep breath as you continue letting him fuck your face until he finally sputters and releases, coating your throat. You swallow all you can as he continues releasing and you swallow until he goes soft. You lick up and around catching the rest and then look up at him with lidded eyelashes. 

He smiles. “Damn sweetheart. That was great.”

You tuck him back in his boxers, zip and button up his pants. Crawling back up to him, he drags you up to him as his mouth ravages yours and he tastes himself on your tongue. His hands are back to your rear end, squeezing your buttocks. He gets up as you wrap yourself around him again. “Bedroom?”

“Last door on the left.” He walks down the hall. He leans you against your closed bedroom door and presses himself into you, and you can feel his bulge beginning again.  _ So soon? _

He opens the door, walking in and kicking the door shut behind him. Reaching your bed, he lays you down towards the end and smiles. Pulling off his jacket and tie, he tosses them to the chair, drops to his knees and smirks. “My turn for dessert.” His face looks downright sinful.

He raises your dress over your waist, leans in spreading your legs as he begins kissing your inner thighs. 

“Oh God!” You haven’t been touched like that in so long. By the time you broke up with Joe, it had been 2 months since you last had sex and so over a year and 2 months later, you are being pleasured better by a stranger than you did from someone who supposedly loved you. 

“I loved the fact that you ordered a burger,” Dean said as his lips caressed between sides. “I love that you don’t care what you should or shouldn’t eat. It just makes me want to eat you out so much more.”

He moves your panties over to the side as he makes one long lick from your entrance to your clit. Your breath hitches as he engulfs your clit with his mouth and sucks while he begins thrusting a finger into your entrance. It had been so long since you had an orgasm that he barely got second finger in you before you clenched around him and came. “Oh Fuck Yes Dean!” You’re panting and sweating already. 

He takes a minute to pull your panties down as and moves back so he can work you through your orgasm. You moan in ecstasy. You smile. “Come here.”

Dean moves up kissing you and you taste him and you in your mouth. You begin unbuttoning his crisp white shirt, which isn’t so crisp now as he was wearing your arousal on his shirt. “Your shirt?”

“It’s fine. it’s a Badge of honor.”

He begins pulling up your dress over your head and tosses it to the floor. His hands begin caressing your torso as you run your hands up through his hair, his chest and up and down his back. You feel his muscles of his pecs and biceps; you feel his backbone and muscles as he moves up and down over you. All the while, his lips move from your lips to the crease of your neck as he places little love bites across your skin. 

A finger slips under the strap of your bra as he pulls it down, then does the other side, as his slips under you to unhook your bra effortlessly.

“Damn you’re good.” You smile at him. “I bet you practice a lot.”

He smiles back as he removes the offending clothing, then leans in swirling his tongue around your nipple pulling it in his mouth and he sucks until it hardens. 

“Oh Man!” He’s got you right where he wants you. You reach down as you begin unbutton and unzip his pants, pulling them down. He gets up letting his pants drop pulling down his boxer briefs and steps out of them, reaching down to grab a condom, while you scoot up to the headboard. 

He crawls up the bed as he settles in between your legs and his lips meet yours. One of his hands rests on the mattress near your head, his other one reaches between your legs as he begins rubbing your clit. “Gotta get you to last a bit longer now sweetie.”

You being to moan as you feel his hand applying pressure to the cluster of nerves. Reaching down, he begins pumping a finger in you. You start to feel your walls cave. A second finger is applied and you cry out. “Please.” 

He begins to feel you clench around him. “Not yet Baby.”

He sits up a second to put the condom on and you stare at his girth wondering how you are going to take him all. He smiles as he leans in and kisses you passionately. He adjusts your hips slightly and he enters you moving inch by inch, filling you up. 

You gasp at the way he fills you all the way to the hilt, then gives you a moment to adjust.

“You’re beautiful. You know that?” He looks into your eyes. 

“No.” You look away from his glare, but he touches your chin, you look back at him and he looks deeply into your eyes. “You are beautiful Y/N.” He begins to move. 

You begin your dance. He moves out and back into you as you find your rhythm. His lips meet yours between panting and sweating. You wrap your legs around his waist, changing the angle and he begins hitting your g-spot.

You both begin spewing expletives as your thrusting and bucking become erratic.

“Fuck Y/N.”

“Shit! Please.”

“I’m getting close,” you cry out. 

“Fuck! I’m right here. Whenever you’re ready.”

He begins thrusting into you without abandon as his hand massages your clit. You feel your walls cave and your vision go white as he begins to pulse against your walls. You feel yourself coating him and he shudders and releases in you. 

He collapses against you. “That was fucking awesome.”

“That was pretty incredible.” Your body continues through your orgasms.

He kisses you hard on the lips, then moves down to your neck as he turns you to your sides; he remains in you.

He finally pulls out, discards the condom, rolls to his back and pulls you to his chest where you rest against him. 

“I’ll admit it’s been awhile since I did this. Thank you.” You said it quietly. 

He heard. “Well, You’re welcome. Really? I couldn’t tell.”

“That’s good. I guess it’s like they said, ‘like riding a bike.’”

“I didn’t mind being your first bicycle in awhile.” He smirked. 

He kissed the top of your head as you fell asleep.


	3. Chapter 3

You awoke the next morning feeling like completely used putty. You got ‘back in saddle’ many other times that night. Dean had your body in so many positions that you would have never imagined doing with Joe. 

After the standard missionary of your first time back on the bike, he had you on all fours from behind (which was not entirely unpleasant, but definitely lacked on intimacy), riding him (your favorite), riding his mouth (another favorite and definitely new), and across your computer desk. 

You looked over seeing the dashing FBI agent sleeping on his stomach, his taut back and pert ass bare. He was gorgeous and you feel yourself growing closer to him than you probably should. 

He must have felt your stare because he began to move. You raised the sheet over your bare breasts and smile. 

“Morning.” You realized you said it a little too chipper, but after the night you had, you really couldn’t stop the smile creeping across your face. 

He looked up a little more surly. “Morning.” He grunted laying back down against the pillow. 

“I threw your shirt in the wash sometime last night and will put it into the dryer and take a shower. Then I thought maybe you’d want to catch some breakfast with me. You could text Sam and Angelica to meet us there so I can catch a ride back with her.”

“OK.” He said into the pillow.  _ He doesn’t seem in such a hurry to go. Maybe you shouldn’t be either _ . 

You looked over at your phone to see a text from Angelica. “How was it? Was he good? I need to know you’re OK?”

You text back a simple “I’m alive and feel like putty. It was Epic!”

She responds. “Same here. Damn those boys were taught well. I want details later.”

You laugh. 

Dean hears you laugh. “What’s so funny?”

“Nothing.” You continue giggling as you look at him. You get up grabbing your robe, putting it on. You walk to your laundry room and throw his shirt in the dryer and headed back to your room to the shower. 

You turn on the water as you let it warm, then get into the shower. You let the water fall down massaging your worked muscles. Moments later, you hear tapping on the shower door. “Can I come in?” You see his silhouette through the glass including his erection. 

“OK.” Your breath hitches and you’re trepidatious. It’s one thing with the lights dim, but it’s morning, it’s light out and his beer goggles are gone. You’re going to look completely different and you’re scared it will turn him off. 

He opens the door and you keep your back to him to give him privacy too, but he walks over, leans in, and begins to nibble your shoulder. “Good morning Beautiful.”

“Really?” You didn’t mean to say it outloud, you just did. 

He places his hands on your waist and begins turning you towards him. “Yeah. Really. Why do you think that you’re not beautiful?”

“Because I’m not. I’m heavy.”

“You’re curvy. I like curvy.” He places his hands on your breasts. “You’re breasts are so squeezable.” He kneads them tenderly. You breathe.

He moves his hands down to your hips and thighs as he digs into them. “Big strong hips to wrap around me.” You blush. He then moves to your ass and squeezes your cheeks. “I can get lost in you.” He stares into your eyes. It’s almost unbearable, like he can see through your soul. “I want you.” He then moves down picking up your thighs as you wrap them around his waist and your arms around his neck.  Pushing you against the wall, he presses his lips to yours, lifting and guiding you to his erection, then pushes down to fill you.

“Oh God.” 

“Fuck! Yes,” Dean grunted.

You find your groove as you move with each other. He leans down sucking on a nipple as the water rains down on you two. Before you know it, the steam is filling the entire bathroom as he’s thrusting hard and deep, hitting your g-spot as your bodies provide the pressure to your clit and you’re coming undone around him. You’re crying out each other’s names along with many expletives until he kisses you through the aftershocks, finally pulling out of you and setting you down gently. You’re wobbly from everything, including the heat and he keeps you pressed against the wall until you felt more stable. 

“You OK?”

“Yeah.” Your smile is euphoric, all the endorphins running through body, like being high or drunk… on him; his touch, his body. You want to tell him you love him, but you can’t be this needy for someone already. 

He notices your face is completely giddy and he smiles knowing he made you like this.

You clean off your bodies as he wraps you in a towel and carries you back to your bed. Crawling next to you, he smiles. “I like you Y/N. I’d like to keep seeing you while I’m in town and when I have to be back to town.”

You blushed. “I’d like that.”

He leans in and kisses you rolling you to your back as your hands begin caressing each other, but before you get too into it, Dean was stopped by a call. “It’s Sam. I need to get this.”

“Oh sure,” you said flustered as you rolled over to your back and calmed your heart.  _ He wants to keep seeing me.  _ You smile.

You hear him talking.

“Yeah Sam. I’m still at Y/N’s. Maybe you and Angelica will meet up with us to eat breakfast.” He turns to you. “Where you wanna eat at?”

“Gary’s has good breakfasts.”

“We’ll meet you at Gary’s in about 30 minutes.” He looks at you as he says it. He almost looks disappointed. 

You were too. You would have liked to have more time with him. 

As soon as he hung up, he looks at you. “How long does it take to get there?”

“Five minutes.”

“Good. That gives us twenty minutes for one more round, five minutes to dress and five minutes to get there.” He smiles as he rolls on you as you wrap your arms around his neck and legs around his waist.”

——————————————————————

So, you were twenty minutes late to the diner. You were disheveled, throwing on clothes as fast as you could. Dean insisted on going down on you one more time, which took half of the allotted time. Then you had to repay the favor which extended everything.

He didn’t seem to care he was late as he put his hand on your back when you entered the diner and found Angelica and Sam sitting at a table. 

“Glad you could make.” Sam looked annoyed. 

Dean just smiled. “Sorry. Got sidetracked.” He winked at you and your cheeks went flush. 

Angelica got up and hugged you. “Damn girl. You look like you barely slept.”

“It’s OK. I’m fine. It was all worth it.” You smile as you all sat down. 

The waitress came over with menus. 

Dean looked at you. “What do you suggest Y/N?” 

“I love the biscuits and gravy scrambler. Two full biscuits, with gravy, sausage, green peppers, scrambled eggs, bacon, and cheese.”

“Sounds like a plan.”

The waitress came over. “What are you having?”

“We’ll get two of the biscuits and gravy scramblers, with two coffees.” He was ordering for you both.

Sam furrowed his brows and looked confused at Dean. You saw his look and realized you and Dean have something Sam isn’t used to seeing for his brother. 

The waitress turned to Sam and Angelica. “And for you?”

“I’ll have the egg white omelet, wheat toast, fruit cup, and coffee.”

Angelica smiles. “I’ll have a fruit cup, small oatmeal, and coffee.”

“You guys must have had a good night,” Sam smiled at Dean. 

“We had a good time.” Dean turned to you and smiled. 

When the food came, Dean smiled. “I am absolutely famished. How about you Y/N?”

“Yeah.” You looked down and smiled.

You all ate in silence. You were famished, so you ate like you hadn’t eaten in a week. Dean smiled as he scarfed his food down too.  While you were physically exhausted, you were also on cloud nine.

After breakfast you all headed out. 

Sam walked towards the Impala and Angelica towards your car as you and Dean followed slowly.

“So…” Dean looks at you. “I got some work to do today, but maybe I could come over tonight after I research?”

“OK.” You reach your car. 

Dean leans in and moves the hair out of your face. “See you later.” He kisses you tenderly then walked over getting into the driver’s side of his car. 

You climb into the driver’s side of your car and Angelica sits in the passenger seat. “Jesus Girl. You must have had one Hell of a night.”

You just smile...


	4. Chapter 4

When you arrive back at your house, Angelica sits you down. “I want to know everything.”

“A lady never tells.” You smirk

“No! A gentleman never tells. It’s acceptable that women will gossip. So Dish!”

You sigh. “It was amazing.”

“So. What happened first?”

“Lots of kissing.”

“OK. Good. What next?”

You smile shyly. “I gave him a…”

“Wow Girl! Give me some.” She gives you her fist and you fist bump. 

“Then he carried me back to my room and went down on me.”

“Carried? Damn. He’s strong.”

“Yes. He is.” You recall how safe you felt in his arms.

“OK. So, what missionary? Doggie? Standing?”

”All Three and shower sex.”

Angelica’s mouth gaped open. “Shower? Geez! I totally got the wrong brother.”

You chuckle. “He was unbelievable. He had me doing things that I would have never imagined with Joe. 

“Like what?”

“Like doggie style and riding his face. Doggie was a little weird. Missing some intimacy, but God that angle caused me to orgasm five times.”

“Five?”

“And that was before I rode his face which was so awesome.”

“I’m glad for you Y/N.” Angelica looks at you sincerely. “At least you’re ‘back in the saddle again.”

“What about you?” You see she’s not as excited. 

“Sam was great, but we definitely didn’t have the same connection that you and Dean had. We did it doggie style a few times and against the wall, but it was just sex.”

You felt you and Dean shared more than just sex. You look at Angelica. “You know it was a really long night and I need to take a nap.”

Angelica got your hint. “OK. Call me later or text me if he’s coming over. If he does, have fun. Don’t do anything I wouldn’t do.”

“That doesn’t leave much. See you soon Angelica.” 

She hugs you and leaves your house, getting into her car that was parked in your driveway. 

——————————————————————

Dean returns to your place that evening. You open the door to see him dressed in a pair of jeans, a T-shirt, plaid flannel shirt and a canvas jacket. He’s still devastatingly handsome.

“Hey.” He smiles. 

“Hi.” You let him in. “How was your day?”

“Good. We think we found what we’re looking for and will be closing up the case soon.”

You turn your head away from him.  _ He’ll be leaving soon.  _ Your heart begins to crack. You finally meet this incredible guy and he’s leaving so soon. 

You feel his arm touch your shoulder. “Hey Y/N. Are you OK?”

You force back tears. “Yeah. Sure.”

He turns you to face him and he sees the sadness in your eyes. Before you could stop, tears start to fall. 

“I’m sorry,” you stammer, trying to stop. 

He senses your pain, grabs your face in his hands and kisses you passionately. 

He carries you back to your room as you two decide to stay in for another epic night of great sex. You feel him over you, thrusting into you as your lips continuing meeting over and over.

“Fuck Y/N.” He feels you clench around him and he explodes in you as your orgasms hit together. 

As you lay naked tangled up with him, you think about a future with him. You hope he visits you often, spending time with you for a weekend every few weeks, and then hope for something more permanent like him staying at your house of moving in with him. However, you also try not to be too hopeful. You’re having fun and this may just be a fling. You hear his strong heart beating under your head as your heartbeat begins to match his as you trace lazy circles around his strange sun/pentagram tattoo over his heart. You’ll ask him about that later as his rhythmic heartbeat and warmth lulls you to sleep. 


	5. Chapter 5

Two days later you’re pressed against the side of his car door as his tongue finds yours. Dean stares into your “Thanks for an amazing week.”

“Thanks for your shirt.” You are wearing one of his plaid shirts. You had asked them both to stay at your house for the duration of the hunt and save them money on the motel. You grabbed the shirt and threw it on the morning he was leaving, refusing to take it off. Dean suggested getting you naked so he could have it back, but then he watched you walking around your house in just it and your panties and he said “keep it. Looks better on you anyway.” That didn‘t stop him from fucking you while wearing it on the kitchen counter while you were cooking breakfast for you two. He unbuttoned it but left it on you as he fondled your breasts with his hands and lips. He then thrusted into you as he held you up in the kitchen, his shirt keeping you covered so when Sam accidentally walked in on you two in the kitchen, he didn’t see much. 

“You’re welcome,” Dean smiles. “I’ll get it back next time.”

“Maybe you can trade it out. Then I can get one that freshly smells like you and you get that shirt back.” You wink at him. 

“OK. Sounds like a plan.”

He kisses you one more time tenderly, you hug Sam, and you watch them both get in the Impala and leave. You weren’t sure you would ever see Dean again. While you didn’t know much more than he was FBI, you knew he was a free agent in the romance department. 

—————————————————————

The first four months were amazing. When he wasn’t on a case, Dean would come back and spend almost every moment naked and tangled in your arms, and when he was on a case he called you every almost every night, especially when he was horny.  You tried phone sex with him and he seemed to get off on your voice alone, but you couldn’t. It wasn’t something you enjoyed, but you did it for him. 

“Damn Baby. Your voice drives me wild and makes me cum on command.” You heard him panting in the bathroom of his motel room while he had the shower and sink running to give you two privacy. 

“I’m glad I could help you relieve some stress.”

“I can’t wait to get back to you and fuck you so hard. I need to hear you cum.”

“Don’t worry Dean. I will when you can get back to see me.”

Then just one day, four months down the road, all contact from him came to a crashing halt. Dean never called and never showed up. It was like he disappeared. At first you were worried. You tried calling Dean. After leaving countless voicemails, you tried contacting Sam, but he never called you back as well. You thought maybe they were undercover and could not be contacted, but when weeks turned into a second month, and you realized you and Dean were done. 

While deep down you had somewhat expected this would happen, it didn’t change the emptiness you were feeling that he was no longer interested in you or coming back. He ghosted you. He didn’t say goodbye. He just never came back.

The emptiness took over you, isolating you from your friends and family. 

You were at home, lying on your couch. The TV was on left on a Property Brothers marathon on HGTV when you heard a knock on your door. You didn’t want get up so you didn’t; however minutes later, you heard the door open and Angelica come in. She had used the spare key to enter. “Hey Y/N. What are you doing?” She was always perky.

“Watching TV.” Your eyes were wet. You had been crying again. You saw an 1967 Chevy Impala in a garage on an episode and you immediately thought about Dean Winchester. 

“Oh Y/N. He hasn’t called, has he?”

The floodgates broke and the tears came down. She hugged you. “I’m sorry Y/N.”

“I really thought we had something.” You were mumbling incoherently.

“It seemed you two did too.”

You continued to cry.

“Have you tried reaching him or Sam?”

“Yes. I haven’t heard from either.”

The last time you were with Dean, you both said you loved each other. You recalled the events.


	6. Chapter 6

_ He was nervous as Hell to tell you. You watched as he rubbed the back of his neck as you sat on your couch together. “What’s going on Dean?” _

_ He finally got up the nerve to speak. “So Y/N, we’ve been seeing each other what? 4 months? _

_ You smile. “Yeah.” You remembered the first night fondly.  _

_ “I remember the first time we met and how I don’t know, but I just cared for you from the moment I saw you.” You could tell Dean was shocked at himself for revealing that to you.  _

_ “I did too.” You placed your hand over his.  _

_ “I remember that first night.” _

_ “You were one bike I loved getting back on.” You smiled and he smiled at you.  _

_ He continued to nervously rub the back of his neck as you watched him bite his lip and look at you.  _

_ “I just want you to know.” He smiled. “I love you Y/N.” _

_ You stared in shock at his revelation and you smiled as you looked into his eyes. “I love you too Dean.” _

_ Dean smiled and leaned in, kissing you passionately. You reciprocated as your your mouth opened for his and your tongues fought for dominance. Grabbing you, he pulled you against him. Your bodies were like magnets. _

_ Next thing you know you were both naked, on your sofa as Dean’s tongue was fucking your entrance and his thumb rubbing your clit, as you cried out his name. After you came undone, he carried you up to your bedroom and made tender, sweet love to you. As you laid underneath him, he pulled you up, close to him as he emptied inside you. You felt his love for you, not just sex.  _

_ “Damnit Y/N. I love you,” he confessed again as he stared in your eyes. “I love you so much. I want to take you home to meet your family, and make love to you in your tiny twin bed in the bedroom you grew up in, then have your dad punch me in the face because we were so loud and the neighbors called the police. I want to go to your friends’ houses for parties and find a room to sneak away to where we have a quickie and then join the party like we had always been there. I want you to come stay with me so I can spend all my non working hours in your arms.” _

_ “I love you too Dean.” You look in his eyes. “I want everything you said too, but most of all, I just want you.” _

_ He kissed you then looked at you and confessed his biggest secret. “You know I need to tell you Y/N… I’m not FBI.” _

_ “You’re not?” You look at him and feigned confusion. _

_ “My brother, Sam, and I travel the country and hunt monsters and ghosts; things that go bump in the night. We’ve prevented the apocalypse and fought Lucifer and Michael.” _

_ “The Lucifer? Like the devil, Lucifer? And Michael, like the arch angel?” _

_ “Yes.” _

_ You looked at him. He doesn’t look like a crazy person yet somehow you secretly knew everything he was saying was the truth. You loved him unconditionally. You finally laugh. “I knew you were too fucking hot to be FBI.” _

_ Dean smiled. “You don’t think what I said was crazy?” _

_ You look at him. “Of course I think what you said was crazy, but I’m open to the supernatural. _

_ However, I do think you’re crazy for loving me. I’m not even in your league.” _

_ Dean smiled and looked at you tenderly. “You are in my league.” He kissed you, then kissed your down entire body, telling you everything he loved about your body. “I love your neck and this sweet spot, right here,” he said kissing the crease of your neck inciting a moan from your lips. “I love your breasts,” he said as he puckered his lips around your nipple sucking it until it was hard. You could feel your arousal pooling as you moaned.  _

_ “Oh yes Dean. Please.” _

_ He took the other breast into his hand rubbing the nipple between his thumb and index finger. “I love how you respond to me.”  _

_ You moaned as you rubbed your legs together, looking for friction.  He continued moving his mouth and hands between breasts as you reached your hand down rubbing your fingers across the the cluster of nerves.  _

_ Dean noticed you as he began kissing down your torso. “I just want to press these lips against everything along your abdomen.” _

_ You began to rub faster and Dean was getting turned on with you turning yourself on. “Oh Baby. I love you touching yourself for me.” _

_ “Please Dean.” You breathily moaned. You moved faster, raising your hips up as you desperately began to chase the high. “Please.” _

_ Dean kissed down your abdomen as he reached down to your sex, removing your hand and took your clit into his mouth sucking it hard as he reached up kneading your breasts with one hand. _

_ You raised your hips, writhing against his mouth as you grabbed his hair, pulling him into you further. “Oh Please Dean. Fuck!” _

_ He took his time bringing you to orgasm as he would stop his ministrations and the flicks of his tongue just as you were about to come undone. “Please Dean.” He smiled as you writhed against his mouth and his tongue pressed against the nerves, finally applying the pressure needed to come undone. “Oh Fuck Yes!” _

_ He was then ready to fuck you again, picking you up, carrying you and pressing you against your bedroom wall, holding you up and pounded into you. “I fucking love you Y/N.”  He fucked you hard and deep and you knew you would be sore the next morning, but he released all his emotions into you that night.  _

_ As he curled up against you, making you the small spoon in bed, he whispered sweet nothings in your ear for hours. You made love a few more times that night. He left for a job the next day and that was the last time you saw him.  _


	7. Chapter 7

“Why don’t you come to dinner with me?” Angelica pleads. She hated seeing you so torn up, especially over a guy. But Dean wasn’t just any guy. You loved him. 

“Not the same place Angelica. I can’t ever go back there.”

“Sure. Let’s just go out to eat.”

“OK. Sure.” 

You drove to the local Mexican restaurant and the first thing you ordered was the XXXL Margarita. You chugged it down like you were in a contest. You ordered another. There was a local patron who bought your drinks, hoping he would secretly get lucky with you, but you shut him down quickly calling him “cute in an old man sort of way.”

Before dinner was served, you were on your third margarita and you were hammered. Angelica took you home. When you got in your house you were stumbling and whining. 

“Dean is an asshole,” you said slurring your words and stumbling to the couch. “I’m going to call him and tell him exactly that.”

“Uh Y/N. Maybe that’s not a good idea.” 

“Well, I think it’s a great idea.” You slurred, getting out your phone and began looking up his number. Dialing the number, the phone rings until the voicemail kicks in. “This is Dean. You know what to do.”

“Dean Winchester. This is Y/N. You might remember me. We met in (Your City) six months months ago. You were the one to get me back in the saddle. We were together four months, when you told me you loved me and then just ghosted me. I just wanted to let you know that You Sir. Are. An. Asshole.” You paused between each word. “You know I really thought we had something, but obviously I was just a four month fucking fling.”  Your anger and changed to crying. “Well, I’m calling to say I’m no longer a fucking bootycall Dean Winchester. Have a nice life asshole.” You hung up. The weight of your words and the alcohol finally hit you. “I think I’m gonna be sick.” You got up running to your bathroom just in time to wretch. Angelica followed you sitting on the edge of the bathtub as you vomited and cried. “I feel like such a fucking schmuck.”

Angelica looked at you. Her face was almost as sad as yours. “I’m sorry Y/N. I just wanted you to have some fun and get out since Joe, only to get another one just like him. I really thought Dean was different too. I saw how he was with you. I was here a few times he would come to visit you. I remember how loving he was with you.”

“Obviously, he changed his mind.” You were bitter.

“Maybe his job is preventing him from getting to you?”

“He can call or text me. Let me know he is alive.”

“You never know Y/N.”

“Whatever,” you said passing out.


	8. Chapter 8

Dean stumbled into the bunker along with Sam and Cas. “We’re glad you’re safe Dean,” Sam said.

“I’m glad to be back. I’m glad we got that blue eyed Sonofabitch out of me. I can’t wait get to tell Y/N.” He smiled.

Sam frowned.

“What’s wrong? Have you heard from Y/N?”

“Yeah we have Dean.” Sam walked over setting Dean’s phone on the table. “You might want to listen to this.”

He picks up his phone and begins to play his voicemails. At first the messages from you were sweet and concerned. He smiled, but also was sad to know you cared about him and he was gone. Then he got to the last one and he listened to the full message. When the message was done, he looked down at Sam angry. “You mean no one had the decency to call Y/N to let her know I was missing. She said she called you a ton Sam.”

“Dean,” Sam looked at his brother angrily and anguish. “I didn’t answer her because we were looking for you, searching everywhere. I’m sorry I didn’t have time to let some fling know.”

Dean was pissed and stared at Sam. Anger radiated off him. “Dammit Sam. Y/N was not just another fling to me. I love her. I told her I loved her the weekend that I got captured by Michael’s army.”

Sam saw the anguish in Dean’s eyes. “I didn’t know Dean.”

“You knew I was spending all my downtime from hunts with her.”

“Yeah.” Sam looked down.

“I’ve got to go see her; tell her I’m back. She probably thought I just left her.” Dean got up.

“Wait Dean,” Sam said. “We need to find out where Michael is.”

“I need to see Y/N.”

Dean walked back his room where he packed up his bag. He headed back through the bunker.

“Dean. This isn’t a good idea.” Sam looked at his brother with concern.

“Dammit Sam. I love her. I was about to ask her to come back here and move in. I need her.” He realized what he just said and his shoulders sunk. “I need her Sammy.”

Sam looked at Dean exasperated and realized his brother was in love. “Ok Dean. Go get her.”

“I’ll get her and bring her back.”

——————————————————————

You were going on date number three with Matt that night. You met a few weeks ago as blind dinner date at Angelica’s house. She insisted you meet him as he was someone she knew for a previous job that she thought would be a good choice for you. He was a few years older so, he was definitely more mature and not someone who will probably date you for four months and then ghost you. He wasn’t Dean attractive, but who ever would be. Dean was dreamboat, absolutely beautiful, and you were way out of his league. The fact you even got the time with Dean amazed you. You knew you were never going to get another Dean and you had to learn to settle.

You had a nice conversation with Matt at Angelica’s and he asked you out. Your second date was dinner and a late movie, which you met at the theater. You seemed to enjoy the same things. He was a gentleman, walking you to your car and giving you a hug.

This third date would be the deal maker or breaker, so you specifically bought another black dress, because you could never wear the dress that you wore when you met Dean ever again, staying in the back of your closet, out of sight. Matt came and picked you up in his older Porsche 933, a car he said he had always wanted and just recently acquired. You confessed you always wanted a Porsche 933 too. You laughed at the fact this the Porsche 911 and 933 were your dream cars when you were sixteen.  Matt was attractive with sandy blond hair, 5’ 10” and a medium build. He complimented you on your dress, staring at your cleavage, which made you blush. He took you to a quaint Italian restaurant where you had a large portion of Fettuccine Alfredo con Chicken and broccoli and he had a Parmesan Chicken. The conversation was good as well as the food and wine. You only had one glass with your meal to remain sober. After dinner, you went to a local club to listen to a local band you both liked. You had a margarita there and enjoyed the music. When he walked you out to the car after the show he smiled as you leaned against the car. “May I kiss you,” he asked.

You smiled and nodded yes. He leaned in as his hands pressed on your shoulders and his lips met yours. They were thinner lips, not like Dean’s. You didn’t feel the neediness or expertise of Matt’s lips that you felt with Dean, but the kiss was short and sweet as he pulled away and smiled. “I like you Y/N. I’d really love to get to know you better.”

You weren’t sure. He wasn’t Dean. He would never be Dean. No one would ever be Dean and you realized you would need to move on. However, this was not the night. “I like you too Matt and I’d like to see you a bit more before we become physical.”

He looked down. He did not like your answer. He opened your door and you got in as he got in the car, started it up and headed back to your place. “I understand Y/N. Angelica told me you just got out of a relationship and so did I.”

“Thanks for your understanding Matt.”

When he pulled up to your house, he came around, opening the door for you as you got up and headed to your door. “Thanks for a lovely evening Matt. I had a nice time.”

“So, when can we see each other again?”

“Maybe in a few days.” You smiled.

You started to open your door and walk in, but before you could shut the door, he stuck his hand out and grabbed it pushing it open. “You are such a little slut,” Matt said in a sinister way. “I heard about you fucking some guy the first night you met him but you make me wait now four dates?” His eyes were callous and angry. You tried to push on the door to shut it, but he pushed it open, pushing you back and onto the floor.

“You don’t want to do this Matt.” You didn’t hear the loud muffler sound pulling into your driveway.

“You are a stuck up fat ass bitch, but Damn you have a nice pussy. You see Y/N, I know Dean Winchester. I know how much Dean loves you and how much he wants you. In fact, he wanted you to move in with him. Was going to ask you soon. He actually saw himself marrying you.” His eyes turned solid black and you backed away more. “I watched you guys for awhile. I mean this guy was always going down on you every chance he got, and then he would fuck you in your bed, in the shower, against the wall, on the sofa, on the floor, in his car, and even on the kitchen counter. I’ve seen everything he’s seen, and I mean everything. I kinda want some for myself.”

He began walking towards you as and you were panicked, crawling backwards on the floor. “I think the only way I will ever get to Dean is by killing his brother, Sam, his precious angel friend, Castiel, and mostly… you. And you are much easier.” He moved closer.

“Get away from her you black eyed Sonofabitch.” Dean pushed open your door shaking a flask as liquid flew out, hitting Matt as he began to wail and flail around like he was burning.

Dean begins speaking in tongues as Matt seizes. It was a long chant. Finally, Matt throws his head back and black smoke billowed out of his mouth and up in the air swirling the air.

Dean grabs you quickly holding his hand around your mouth and nose. “Close your eyes and trust me.”

You were looking around.

“Do it,” Dean snarled.

The smoke rushes around you and him getting awfully close to you. You were grabbing Dean’s arms and hands, trying to pry his hands away so you could  breathe. You were beginning to get light headed. The smoke continued surrounding you, but finally rushed out of your front door. Dean quickly uncovers your mouth as you are gasping for air thinking he was trying to suffocate you.

You bent over coughing and choking. “What the fuck Dean?”

He moved closer and pulls you into his chest, patting your back as you take deep breaths. “I’m sorry. I’m so sorry Y/N. I didn’t want you to get possessed.”

“What the fuck was that?”

“Demon. You OK?” Dean pulls back to look into your eyes, but you instinctively moved back, pulling away from him in fear. What you just witnessed scared the shit out of you and now you are staring at the man you said you loved, but he scared you.

“Dean?” You were confused.

“Yes. It is me.”

“Is it true what Matt said.”

“Yes. I was unable to get to you.”

“What about the other part? The part about loving me.”

Dean’s cheeks began to turn pink. “Yes. I still love you.”

“Were you possessed by a demon?”

“No. An Angel. Archangel as a matter of fact, a bad Sonofabitch that is a hundred times worse than demons.” He looked at you.

You sat down on your sofa. He closed the door, locking it and the deadbolt, and looked at you. He walked over sitting in a chair close to you, but far enough away because he sensed your fear. “I’m sorry Y/N, for being away from you for so long. I promise I would not have left you intentionally. I hope you know that”

“I didn’t know that.” You looked at him confused. “I’m not even in your league.”

“Y/N! How many times do I have to tell you, you are?” He said angrily, but then softened his tone.

“Dean. You just ghosted me. I didn’t know if you were alive or dead. Sam never responded to me neither.”

“He was looking for me. I’m sorry he did not contact you. I’m pissed at him for that, but he was looking for me. It was a difficult time.” Dean leaned towards you. “I’m sorry I got you involved in my life and my line of work. I love you, Y/N, and I want to stay with you.”

You looked at Dean and breathed heavily, tears began to roll down your face. All this time you thought he was just gone and you realize he was trying to get back to you. Dean bridged the distance to you as he grabbed you in his arms and pulled you to his chest. He pressed his arms against your back as your arms wrapped around him. You were panting as your heart was beating erratically. He made you nervous. You breathed in his musk as you felt his heart beating erratically in his chest and his breathing became ragged. He was nervous around you too.

He finally pulled away from you looking deep into your eyes. Reaching up, he tucked your hair behind your ears, as he reached up and pressed his palm to your cheek. “I love you.”

You stared into his emerald green eyes as you felt every molecule in your body was in love with him, and you also knew every molecule in his body loved you. You raised yourself on your tippy toes as you pressed his lips to his….


	9. Chapter 9

You leaned up engulfing his mouth with your lips as his hands slid up your shirt and kneaded your breasts. “Mmmmm.”

You were in your bed as your hands reached around squeezing Dean’s buttocks as he let out a groan. “Oh man. Y/N.” He leaned in kissing you with more need as he pressed his bulge to your mound. “Oh man. I missed you so fucking much.” Dean pulled his plaid shirt off, then peeled his shirt off quickly.

You saw his bare chest and missed him so much. You gripped his bare biceps, down to his hips as you reached your hand down, unbuttoning his jeans, and you slipping your hand down the waistband of his jeans gripping his cock needily. “I want you inside me. Now.”

He looked at you desperately. “Oh God Yes.”

He quickly pulled down your skirt, grabbing your panties and pulling them off faster than he ever had with you.

He yanked his pants and boxers off, while you pulled off your blouse and bra. He reached down pumping his cock a few times as he leaned into you and pushed himself inside you to the hilt. “Oh Fuck Y/N. I missed you.”

You squealed as your breath hitched and you felt him fill you up. “Oh God Dean. Fuck Yes! Move.”

He pulled out and thrusted back in you hard and quick. You cried out again as you felt your body buck to him as he continued thrusting into you.

Your hands shook as you traced your hands over his back muscles and he shook as his lips curled around your nipple and he sucked hard as his cock began to jerk getting ready to cum.

It was like your body knew he was ready as you clenched around him, milking him as he spurted his hot cum deep inside you. “Fuck Yes,” you cried out as you came undone around him.

“Oh Fuck Baby. I love you.” He looked down in your eyes as you felt your entire body just give into him. He leaned in as his lips and tongue met yours tenderly.

“I love you too Dean.”

He stayed in you, as you continued to flutter around him, the aftershocks of your orgasm washing over you both continuously...

——————————————————————

A year down the road and it was a typical Friday night for you two. You were living with Dean and Sam in the Men Of Letters bunker in Lebanon Kansas. You were lying back against Dean’s chest as you laid on the sofa in Dean’s man cave watching an action movie. “So, what are we gonna name him?” You said to Dean smiling.

“I don’t know. What’d you choose?” He smiled down at you as he leaned in and kissed the side of your neck.

You smiled as you looked up and touched Dean’s cheek. “Maybe Bobby after the man you said was like a father to you and Sam when your father couldn’t be. It’s a cute name.

 

“I like it Y/N. What about you?” Dean looked down towards your lap, where a chocolate lab pup was curled up licking your hand. The puppy looked up at you and his tail began to wag.

“Ok Bobby it is.” You were petting the puppy as he fell asleep. You then leaned back as Dean leaned down and met your lips.

  
  
 

**Author's Note:**

> Thanks for reading.  
> If you enjoy what you read, leave a comment.  
> Constructive Critcism appreciated and accepted. Thanks for taking out the time to read and respond.
> 
> Please do not copy, repost or disseminate in any program, website, or forum without expressed written consent of the author.


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